Unless you were born and raised on a ranch, cowboy boots can be notoriously difficult for the average guy to pull off without looking like a (rodeo) clown. But that doesn’t mean you shouldn’t try, especially since they’ve become a menswear must-have.
“It’s no longer cattlemen and ranch hands picking up the boots, but fashion-savvy guys wearing them on the streets of New York, Paris, and everywhere in between,” New York City-based fashion stylist Seppe Tirabassi tells Men’s Journal. “At the moment it’s very on-trend, but it will always remain a timeless footwear staple rooted in genuine American craftsmanship.”
Not all Western-style boots fit inside the cowboy category—they’ve got to tick a few boxes that help their wearers be saddle-ready, per their original purpose. True cowboy boots come with a rounded or pointed toe, originally designed to help the foot enter a stirrup. They also must have a Cuban heel (the fancy name for a straight, medium-high heel with a slightly curved back), which keeps the shoe secure once it’s in the stirrup. Cowboy boots have a high shaft that makes them easy to pull on, and you’ll never ever see laces or any other embellishment that could get caught on something while riding a horse. Lastly, they’re always constructed with durable material—mostly tough leather—that can protect the wearer’s feet from brushes with barbed wire, animals, dust, dirt, and all kinds of other obstacles a cowboy might face.
One variation on the classic cowboy boot is the roper. It’s essentially a streamlined modern version of the cowboy boot with a lower heel and shorter shaft. It was created for steer wrestlers at the rodeo who needed to run faster on foot. No matter what style you choose, however, cowboy boots are timeless—and they get better with age.
“Cowboy boots are an iconic piece of the Americana wardrobe that are made to last a lifetime,” Tirabassi says. “And the more beat-up they look, the cooler they are. Second-hand boots can command even higher prices since customers are really going after the worn-in appeal.”
Below, Tirabassi picked 16 pairs of cowboy boots from his favorite bootmakers and recommended foolproof ways to style them. Time to saddle up.